6364-05-2Relevant articles and documents
CO2-tuned highly selective reduction of formamides to the corresponding methylamines
Chao, Jianbin,Guo, Zhiqiang,Pang, Tengfei,Wei, Xuehong,Xi, Chanjuan,Yan, Leilei
supporting information, p. 7534 - 7538 (2021/10/12)
We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.
Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines
Nishizawa, Akihiro,Takahira, Tsuyoshi,Yasui, Kosuke,Fujimoto, Hayato,Iwai, Tomohiro,Sawamura, Masaya,Chatani, Naoto,Tobisu, Mamoru
supporting information, p. 7261 - 7265 (2019/05/16)
Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.
Direct Borylation of Tertiary Anilines via C-N Bond Activation
Cao, Zhi-Chao,Li, Xiao-Lei,Luo, Qin-Yu,Fang, Huayi,Shi, Zhang-Jie
supporting information, p. 1995 - 1998 (2018/04/16)
The first successful catalytic borylation of unactivated aromatic C-N bonds of tertiary anilines without the preactivation or any directing groups is demonstrated. The reactivity of both N,N-dialkylarylamines and N-arylpyrroles were investigated systematically, and the targeted products were furnished in moderate to good yields. The DFT calculation results indicated that the catalytic cycle is furnished via a five-membered cyclic transition-state due to the steric hindrance of the Ni/NHC catalytic system.